Search Key West Cottages

Compare Cottages in Key West with updated reviews, rates, and availability.

Beach nearby
Southernmost Retreat: 2 Blocks from Duval in Old Town.
10.0 out of 10, Exceptional, (98)
"Walking close to Duval. On street parking can be tough but this block is NOT pay to park! Good to know."
Southernmost Retreat: 2 Blocks from Duval in Old Town.
Exterior
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
10.0 out of 10, Exceptional, (118)
"Loved this property! Will definitely be staying here again! Location. Location! Location!!"
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
Interior
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
4.5 star property
10.0 out of 10, Exceptional, (3)
"The unit had fun and stylish decor. Bed was comfy and I’m picky. The steeps are a challenge- always forgetting there is one more step. Was concerned about the noise in the back from a restaurant or bar- but when doors closed you can’t hear it. And there is no noise later in the evening. One suggestion- some nightlights for the night for Safety. We will be back. Great experience "
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
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Fridge, microwave, oven, stovetop
BLUE BIRD ~ Adorable 1 BR, 1 Ba Conch Cottage in Bahama Village!
10.0 out of 10, Exceptional, (1)
BLUE BIRD ~ Adorable 1 BR, 1 Ba Conch Cottage in Bahama Village!
Interior
Atlantic Paradise by Avantstay Great Location w/ Balcony, Outdoor Dining & Shared Pool & Hot Tub!
3.0 star property
10.0 out of 10, Exceptional, (1)
"Extremely clean, quiet and spacious. The friendly. staff and location to the water made the five day girl’s trip so fun. Thanks. "
Atlantic Paradise by Avantstay Great Location w/ Balcony, Outdoor Dining & Shared Pool & Hot Tub!
Pool | A heated pool
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
10.0 out of 10, Exceptional, (195)
"This beautifully decorated property is centrally located but feels secluded. The beds are incredibly comfortable and the pool was perfect for relaxing. It was perfect for our girls' weekend. The property manager was attentive and helpful. We would definitely stay here again."
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
Beach nearby, beach towels
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex
10.0 out of 10, Exceptional, (169)
"This was our 4th trip to Key West and our 2nd stay at this property. We had 6 adults (age 59 - 89) both times and it really did fit our needs. Great location for everything (bars, coffee shops, restaurants and shopping) we like to do and go as we don't spend a lot of time staying at the property except to take a break and rest. This property is relaxing and quite and love sitting on the decks in the morning having coffee, reading and listening to the roosters."
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex
A heated pool
Quaint Pool Cottage in Old Town Key West Great value
10.0 out of 10, Exceptional, (4)
"Great little house. Walking distance to pretty much all of old town area. Has a nice pool to relax in. HUGE bathroom. Bedrooms are nice sized. Washer/dryer is a huge plus for long stays. The only thing - wish it was closer to the beach…"
Quaint Pool Cottage in Old Town Key West Great value
Outdoor pool
Uptown quiet cottage close to beaches, restaurant & shopping.
10.0 out of 10, Exceptional, (2)
"Friendly courteous communicative host. Clean comfortable location away from the noise and hustle of Duvall but easy bike to Duvall. The bed was very nice!"
Uptown quiet cottage close to beaches, restaurant & shopping.
Interior
Coral Villa by Avantstay Close 2 DT Key West Shared Pool & Patio!
3.0 star property
10.0 out of 10, Exceptional, (1)
Coral Villa by Avantstay Close 2 DT Key West Shared Pool & Patio!
Interior
Amelia Home by Avantstay In Historic Old Town w/ Pool
3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was amazing, much more than we expected. We loved the pool area and the landscaping, both were maintained beautifully. The whole place was clean as a whistle!"
Amelia Home by Avantstay In Historic Old Town w/ Pool
A heated pool
PINEAPPLE COTTAGE ~ Adorable, Updated Cottage in Old Town with Heated Pool!
9.8 out of 10, Exceptional, (12)
"Overall great. Loved location. Friendly locals enhanced experience. Only complaint was with mid stay clean that was required. Suggestions for mid clean- Should be different in some ways than final clean - - - - I’d set time on coffee pot so could set up night before and have coffee ready in am. Was unplugged during clean. Making me have to reset time again. Blender/toaster set out on counter to use without having to get down on floor to retrieve them from small cabinet between stove...
PINEAPPLE COTTAGE ~ Adorable, Updated Cottage in Old Town with Heated Pool!
Fridge, microwave, oven, stovetop
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
9.4 out of 10, Exceptional, (199)
"Close to everything but just far enough away to be quiet and relaxing. Cute little house. Very walkable location."
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Pool
Conch Republic Consul General's Cottage.-Historic District
9.4 out of 10, Exceptional, (136)
"The house has a lot of potential but very dated. First two days AC was broke and the fan in the master bedroom had no pull chain. Too hot for no air flow. The master bed was so old it squeaked every time you moved. Also mattress was too firm. The positives were the property cat and the location."
Conch Republic Consul General's Cottage.-Historic District
Property grounds
Conch Republic Consul General's Cottage.-Pool-No Contact Check-In
9.2 out of 10, Wonderful, (66)
"We really enjoyed our stay here. There was ample space, especially for a couple. The location is excellent, close to Duval St., beach, or southernmost area. We rang in the new year while staying here and the access is easy, well lit, and off street parking for one vehicle. The kitchen was stocked with what you’d need to prepare a meal, full size fridge is a plus, and microwave and stove. The only thing to point out is the shower is cramped and I’m a tall guy. The shower worked great and had...
Conch Republic Consul General's Cottage.-Pool-No Contact Check-In
Beach
Tranquil Dog-friendly Getaway with Shared Pool, WiFi, & AC - Snowbirds Welcome
9.0 out of 10, Wonderful, (164)
"Lovely home! Fabulous location near the dog beach and restaurants on the beach! Convenient f oh r exploring the island!"
Tranquil Dog-friendly Getaway with Shared Pool, WiFi, & AC - Snowbirds Welcome
Property grounds
Maryann's Place - Large Monthly Studio (New Listing)
9.0 out of 10, Wonderful, (4)
"I drove down with my vehicle for one month in March for a "work"-cation - primarily me, then my father visited the final week. The property is nestled in a quiet, suburban neighborhood, with a relatively short walk to Higgs Beach (south shore) and a longer walk to downtown/Duval Street. The property is clean, well-maintained, and had all essentials (toilet paper, paper towels, sponges, dish soap, salt/pepper, pots/pans, etc.) initially stocked as described. Technically on shared property, you...
Maryann's Place - Large Monthly Studio (New Listing)
Outdoor pool, a heated pool
New Conch cottage, with heated pool, walking distance to downtown Key West.
8.0 out of 10, Very Good, (1)
"This semi detached 1BR/1 Bath home is perfectly situated in the best kept secret for long stays in Key West - the White Street Gallery District. White Street is the most amenity rich street in Key West. From it's beautiful pier to the south right up to it's north end, White Street offers just about everything you would ever need. This home is located across from Bayview Park, which hosts numerous events throughout the year. There are basketball courts as well as tennis courts and childrens...
New Conch cottage, with heated pool, walking distance to downtown Key West.
Exterior
Old Town Cottage House in Old Town Key West!
Old Town Cottage House in Old Town Key West!
Interior
Key West Found by Avantstay Close to Shops w/ Patio & Shared Pool! Week Long Stays Only
3.0 star property
Key West Found by Avantstay Close to Shops w/ Patio & Shared Pool! Week Long Stays Only
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Key West

Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (16)
"My son and his new wife stayed here for their honeymoon and they absolutely loved it!"
Poolside Cottage #411
Beach towels
Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, (330)
"My husband and I just got back from Key West. We had a fabulous time and loved where we stayed. Ken, the owner, is terrific. Great communication, excellent tips on things to do and places to eat. It a large house and you have a room to stay in with your own bathroom, small kitchen and bed. It was perfect for us. We will definitely be back next time we visit Key West. Thanks Ken for being a great host!!!"
Steps from Duval, Pool & Bikes $129-$299 Night!
Outdoor pool
Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
8.4 out of 10, Very Good, (228)
"Perfect location - not to far of a walk from Duval Street and the action but tucked away just enough to be able to have some peace!"
Hyatt Vacation Club at Sunset Harbor, Key West
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Key West Cottages information

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Frequently asked questions

How much do cottages in Key West cost?
Cottages in Key West range between and per night. These retreats offer a chance to get reacquainted with nature — at a price you can afford. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best cottages in Key West?
A traveler favorite is Simonton Court Cottages. Make yourself comfortable at this 3.5-star stay which comes with a garden and a nearby beach. Simonton Court Cottages is another recommended option worth shortlisting. Unpack your suitcase at this 3.5-star cottage and you’ll have access to amenities such as free WiFi and pet-friendly facilities. You can choose from multiple cottages in Key West with a total average guest review rating of .
How many cottages are there in Key West?
Pack your suitcase and pick from cottages in Key West. Dreaming of a place where you can relax and stay in touch with nature? Expedia can help you find the ideal getaway in a few quick clicks.
Are there any family-friendly cottages in Key West?
Many visitors searching for a family-friendly cottage in Key West choose Simonton Court Cottages. With a 3.5-star rating and amenities such as a nearby beach and free WiFi, you’re sure to feel right at home here. Another noteworthy pick for families on vacation is Simonton Court Cottages. Free WiFi and housekeeping services help make this 3.5-star cottage a great base for your Key West trip. Key West boasts loads of family-friendly attractions to visit when the kids are getting restless. Smathers Beach and South Beach promise a fun day out for travelers of all ages.
Why book your cottage in Key West with Expedia?
Reserving a cottage in Key West is as simple as deciding on your travel dates and selecting your ideal place for a vacation in the outdoors. From high-end retreats to budget-friendly properties and cottages that include amenities like a kitchenette, Expedia has something for all tastes. As for the best offers around? We’ve got them as well!
How can I find cheap cottages in Key West?
The easiest way to get cheap cottages in Key West is with Expedia’s filter tool. Refine your search by star rating, amenities and budget to access unbeatable deals in a couple of clicks.
What is there to do in Key West near my cottage?
Key West has enough experiences and sights to keep you occupied for weeks, beginning with Smathers Beach. South Beach, Fort Zachary Taylor Historic State Park and Higgs Beach are other popular attractions. If you’re hanging around a while, Key West Aquarium and Boca Chica Nude Beach will put the finishing touches on your itinerary.

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